4-OXOCYCLOHEXANECARBONYL CHLORIDE synthesis

3synthesis methods

Product Name:4-OXOCYCLOHEXANECARBONYL CHLORIDE
CAS Number:914637-80-2
Molecular formula:C7H9ClO2
Molecular Weight:160.6

874-61-3
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914637-80-2
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Yield:-

Reaction Conditions:

with oxalyl dichloride;N,N-dimethyl-formamide in dichloromethane at 20;

Steps:

C-01.a1

Oxalyl chloride (0.89 g, 7.0 mmol) and a few drops of dry DMF are added to a stirred solution of 4-oxo-cyclohexanecarboxylic acid (0.50 g, 3.5 mmol) in CH₂Cl₂ (7 ml) and the reaction is kept stirring at rt overnight. The volatiles are removed under reduced pressure, the residue is azeotroped with toluene and dried under high vacuum yielding crude acid chloride. This material is reacted without further purification with N-methylaniline (0.16 g, 1.5 mmol) in CH₂Cl₂ (7 ml) in the presence of DIEA (0.58 g, 4.5 mmol). After stirring overnight at rt, saturated aqueous NaHCO₃ is added and the mixture extracted three times with CH₂Cl₂. The combined organic layers are dried over Na₂SO₄ and evaporated. The residue is column chromatographed on silica gel (hexane/ EtOAc 2:1) and the title EPO compound is obtained as a pale yellow solid (0.47 g) in 57% yield. X_R (LC-4) 0.89 min; ESI-MS (positive ion): m/z 231.98 [M]⁺ (calcd 231.13 for C₁₄Hi₇NO₂).¹H-NMR (CDCl₃): 2.04 (m, 6H); 2.45 (m, 2H); 2.65 (m, IH); 3.28 (s, 3H); 7.22 (m, 2H);7.44 (m, 3H).

References:

WO2006/70325,2006,A2 Location in patent:Page/Page column 72-73

6297-22-9 Synthesis

6297-22-9
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914637-80-2
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References

17159-79-4 Synthesis

17159-79-4
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914637-80-2
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References